Work was performed towards the synthesis of the achiral portion of the antitumor
antibiotic lactonamycin. It was proposed that this would be accessible via a novel
cascade reaction utilising either transition metal, or radical protocols. A model system
was devised, synthesised, and the cascade reaction successfully performed using radical
chemistry. Upon heating the cascade precursor in a thermal decomposition study, it was
found that the cyclisation proceeded via a thermal mechanism and that no radical or
heavy metal additives were required. Investigations into this noyel cyclisat~on reaction
were undertaken through the use of analogues and several reaction mechanisms
postulated. Further work on aromatisation of the lactonamycin model system was
undertaken and a possible synthesis of the achiral portion of lactonamycin proposed as a
result.